Methyl 3'-nitro[1,1'-biphenyl]-4-carboxylate → methyl 4-(3-aminophenyl)benzoate

HRID 1449507Notes

Reaction equation

HRID 1449507 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([C:10]2[CH:15]=[CH:14][C:13]([C:16]([O:18][CH3:19])=[O:17])=[CH:12][CH:11]=2)[CH:7]=[CH:8][CH:9]=1)([O-])=O>O1CCCC1.[Pd]>[NH2:1][C:4]1[CH:5]=[C:6]([C:10]2[CH:15]=[CH:14][C:13]([C:16]([O:18][CH3:19])=[O:17])=[CH:12][CH:11]=2)[CH:7]=[CH:8][CH:9]=1

Participants

4

Reactant 1

HCID 2753361Methyl 3'-nitro[1,1'-biphenyl]-4-carboxylate

Product 1

HCID 1393986methyl 4-(3-aminophenyl)benzoateYield 98.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

In 100 ml of tetrahydrofuran was dissolved 2.70 g of methyl 3'-nitro-biphenyl-4-carboxylate obtained in Reference Example 8. To the solution was added 1.0 g of 10% palladium-on-carbon and the mixture was subjected to catalytic reduction for 2 hours. After removing the catalyst by filtration, the solvent was removed under reduced pressure to obtain 2.34 g of the titled compound.

Workup

  1. customobtained in Reference Example 8
  2. customAfter removing the catalyst
  3. filtrationby filtration
  4. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-da207b51dff04d0497f68fd1ffe0089e
Source dataset
uspto-grants-1997_02
Patent number
US05599813

Reaction notes

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